


monkey see, monkey do

by Anonymous



Category: Supernatural
Genre: Accidental Voyeurism, Anal Sex, Bottom Dean Winchester/Bottom Sam Winchester, Double sided dildo, F/F, Hand Jobs, Plot What Plot/Porn Without Plot, Sex Toys, Sibling Incest, Trans Female Character, Trans Female Dean Winchester, Trans Female Sam Winchester, late seasons first time
Language: English
Status: Completed
Published: 2021-02-20
Updated: 2021-02-20
Packaged: 2021-03-17 07:15:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,682
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29589180
Author URL: https://archiveofourown.org/
Summary: Where Dean watches Sam, and follows her motions.or unabashed trans fem wincest porn
Relationships: Dean Winchester/Sam Winchester
Kudos: 8
Collections: Anonymous





	monkey see, monkey do

**Author's Note:**

> *disclaimer* I used he/him pronouns when referring to Sam and Dean as kids, or before they realized they're trans.
> 
> enjoy!

Dean's 36 year old little sister started first. Sam came out to Dean, over drinks late at night in the bunker. She then reminded him in the morning.

"No more Samantha jokes, Dean. It's still Sam."

They were the Winchester siblings. Question it in front of them, you'll get two guns pulled on you.

Sam was always throwing Dean for a loop, this time it was in a good way. 

He kept thinking about it, what she said to him about how they grew up. About how she realized this for herself, before realizing some things for himself.

Dean starts a few years after Sam. The deadliest hunting duo, the Winchester Sisters, feared by the heroes and villains alike.

Sam used to follow Dean around, copying her ever since they were kids. Now Dean was following her.

"Monkey see, monkey do," Dad had told him, when Sammy broke his arm jumping after Dean off the roof. "You need to set a good example for your brother Dean. He watches everything you do. Sam'll follow you off a cliff."

  
  


34 years later Dean stood in front of Sam's door, watching her.

She supposed Sam believed she had the time to get herself off before Dean came back. Cas and Jack were on a run of the mill haunting case, and Dean went to the bar. She struck out though, none of the women she came up to seemed to click with her, so she came back early.

Early enough to get a show.

Sam had a long purple dildo in her ass. Long enough for her to have more than a handful of it outside of her, tightly holding onto it. Every time Sam's hand moved, pushing the dildo deeper into herself, Dean followed the motion with her eyes. It was mesmerizing, the flush of her skin, the little gasp exhales she released each time she fucked herself.

Dean swallowed, cock stiffening in her pants.

Giving her dick some more room, she shifted her feet wider. Doing so accidentally tapped against the door making it creak all the way open, and Sam looks up from herself to catch Dean looking right at her. 

"Jeeze!" 

She goes to cover herself with the blanket under her, but stops when Dean doesn't move from the door frame.

"Dean?"

"Sam, uh."

Sam narrowed her eyes to get a closer look at her, before widening them in surprise. Dean was...turned on. Her irises were blown from lust, she can only see an outline of green, framed by a high flush on her sister's cheeks.

Sam pushed the blanket back, keeping her eyes locked with Dean's, and opened her legs wider. The blanket brushed against her chest, and she kept her hand there, cupping her breast and thumbing around her nipple until it hardened, gasping at the sensation.

"Sammy..."

"You wanna watch De?"

She had a vice like grip on the door, knuckles white. Sam smirked, and let her hand travel slowly down her body, putting on a show. She needed her older sister's hands on her, and Dean needed some convincing.

Trailing goosebumps behind on her skin, she trails her fingers along her hips to grasp her cock, semi-hard in her hand. One hand still holding her dildo.

"I need you to help me Dean, I only got two hands here."

"Sam." Dean was trembling, need fighting against everything she's ever told herself since she was a teenager.

"Come'er. Please?"

She licked her lips, and Dean's gaze fell to them, finally stepping into the room. Once she's started, she doesn't stop and makes it to kneel on the bed in a few fast paces.

Her hands hover over Sam's skin, unsure. Sam grabs her sister's hand, threading their fingers together and bringing her where she wants her.

"Right here," she has her hold one of her breasts, "you can touch me." She guided her hand to thumb at her nipple, just like how she did it.

"Sammy-" Her eyes watching their hands together.

"Dean." She whispers her name, voice breathless with arousal, and looks back up at her sister.

Sam brings her lips to hers. Dean's hand slides around to hold her side, while her other hand grabs the back of her neck to bring them even closer.

They kiss until it feels like they were sharing the same breath, the same soul.

Dean pulls back first, and Sam gets dizzy breathing in, watching her sister take a shaking breath as well.

Dean pulls back further, and Sam feels a spike of fear, before Dean pulls the flannel down off her shoulders. Sam reaches up, but winces in discomfort when the dildo shifts into a painful position. While Dean is taking her shirt off, she pulls the dildo out of her, getting up on her knees too, to help Dean undress.

Since they've both been transitioning, they've been in various stages of undress around each other. Her sister's tits were nothing new to her. But now where Dean's flush is deep down her chest, contrasting the freckles that travel further than her face too. All of this feels completely new.

Dean's got a dark blue sports bra on, threadbare from use. She sits up to take off her pants. Underneath she was in black briefs that hug snug against her ass, Sam grabs a handful of her, pulling her into her lap.

Sam gets her fingers around the seam of her underwear, wanting to feel more than cotton over Dean's ass. Dean shimmies them off and pulls Sam's hands back down.

She feels along Dean's thighs, coming up to press a dry thumb against her asshole while Dean kisses down her neck.

"Mmh you wanna fuck me Sammy?"

She moans and wraps an arm around Dean's waist, bringing her closer until their cocks were together. She's imagined it, fucking her older sister, but today she was thinking of Dean fucking her. And if Dean wanted it too, she looked to the side of the bed, where she threw the dildo.

"How about we fuck each other?"

Dean stares at her with an open mouth, and Sam couldn't tell if it was shock or arousal. Dean broke into a megawatt grin, and nodded.

Sam reaches over for the lube, and pours a generous amount out into her hand. She spread it around Dean's rim, before slipping her thumb into her. She was so tight and hot, Sam had to get her fingers in her.

She pressed deeply with her thumb, before switching it with her ring and index, thumb around her rim. She keeps pressing until Dean jerks sharply in her arms. Sam keeps the motion there, and Dean melts in pleasure.

She finger fucks her until her wrist gets sore, and Dean taps out, getting close to coming. Sam pulls her fingers out, and grabs the dildo.

Dean takes it from her hand, "Can I put it in you first?" And Sam nods, dumbstruck as hell.

Dean gets off her thighs, coating the plastic with lube, before slowly pushing it into Sam. Her intense gaze, watching Sam's face and watching the dildo go into her. Dean kept whispering, asking to see if what she was doing was good for her. All she could do was nod, moaning out affirmatives.

She nearly closed her eyes in pleasure, but kept them open. She watched Dean watch her, close enough to share air between them, feeling deep inside herself whenever Dean's hand moved.

Sam watches as Dean shifts forward to slowly put the other end of the dildo into herself, holding onto her sister's thigh to steady her. 

As they got closer and closer, the dildo between them disappeared into them, Dean climbed right into her arms. Sam's long legs sprawled around her. Dean brings a hand down and lines their cocks up, wet with excess lube.

Dean is beautiful in her lap, the dildo finally reaching her just right, and she grinds against Sam to keep the rhythm going.

They were thrusting at different times, but similar to everything from hunting to breathing, Sam and Dean got in sync. Sam moaned and reached for Dean's hips, holding onto her, leaning her head down against her neck. Dean brought her other hand up to thread it through Sam's hair, keeping her head there as she started kissing and biting.

Sam goes first, Dean rubbing her thumb through the precome on Sam's cockhead, once and twice. Sam spilled into her hand and on her cock while biting out her orgasm onto Dean's pulse point.

"Oh Sammy, there you go baby sis, god so good for me."

Sam shivers through another crest at her praise, grinding the toy against her prostate, until the pleasure turns bright hot with over stimulation. Moving away from Dean's neck, Dean let go of her cock and started to shift off of her.

"Wait." Sam moves her legs out from under her, pulling herself off the dildo, while holding it to keep Dean's position.

She leans back in, sucking on the bruise and teeth marks she just left, before grabbing Dean's cock and fisting her.

"Come on Dean, lemme see you."

"Need more Sam," Dean rocked her hips, trying to get the dildo to move by herself. 

Sam put her knee on it, finally giving Dean some leverage to fuck herself on it.

"Sam, Sammy." Moaning, Dean rode it harder and Sam twisted her wrist to milk her cock.

"Ride it Dean, yeah just like that."

Her breaths quicken, and she groans out a sob when she comes into Sam's hand. Dean falls boneless onto Sam's shoulder. Sam kisses the top of her head, feeling her hair gel against her lips. She slips out from under her, lets Dean continue into laying on the bed as she gets up to clean her hand.

Dean's pulled the dildo out of herself by the time Sam's got back, and follows Sam using the flannel to clean herself up. She threw it to the floor, and grabbed her sister by the waist to bring her back into bed with her.


End file.
